Asymmetric Friedel-Crafts alkylation of pyrrole with nitroalkenes catalyzed by a copper complex of a bisphenol A-derived Schiff base
TETRAHEDRON, cilt.71, sa.19, ss.2882-2890, 2015 (SCI-Expanded, Scopus)
- Yayın Türü: Makale / Tam Makale
- Cilt numarası: 71 Sayı: 19
- Basım Tarihi: 2015
- Doi Numarası: 10.1016/j.tet.2015.03.059
- Dergi Adı: TETRAHEDRON
- Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
- Sayfa Sayıları: ss.2882-2890
- Anahtar Kelimeler: Chiral copper complex, Pyrrole, Nitroalkene, Asymmetric Friedel-Crafts alkylation, Asymmetric synthesis, INDOLES, ENONES
- Atatürk Üniversitesi Adresli: Evet
Özet
The asymmetric Friedel-Crafts (FC) alkylation of pyrrole with nitroalkenes was mediated by CuBr2 and a novel bisphenol A-derived chiral catalyst at room temperature. The catalyst was found to be applicable for the asymmetric FC alkylation of pyrrole with a wide range of nitroalkenes, affording optically active alkylated pyrroles with enantioselectivities up to 94%. Furthermore, enantiomerically pure 3-nitro-2-arylpropanamides were prepared by the oxidative cleavage of the pyrrole rings in the FC products with NaIO4/RuCl3 to demonstrate the synthetic application of the products. (C) 2015 Elsevier Ltd. All rights reserved.